ATE149152T1 - HYDROGENATION OF META-TOLVENEDIAMINE - Google Patents

HYDROGENATION OF META-TOLVENEDIAMINE

Info

Publication number
ATE149152T1
ATE149152T1 AT94114878T AT94114878T ATE149152T1 AT E149152 T1 ATE149152 T1 AT E149152T1 AT 94114878 T AT94114878 T AT 94114878T AT 94114878 T AT94114878 T AT 94114878T AT E149152 T1 ATE149152 T1 AT E149152T1
Authority
AT
Austria
Prior art keywords
hydrogenation
meta
catalyst
tolvenediamine
support
Prior art date
Application number
AT94114878T
Other languages
German (de)
Inventor
Gamini Ananda Vedage
Original Assignee
Air Prod & Chem
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Air Prod & Chem filed Critical Air Prod & Chem
Application granted granted Critical
Publication of ATE149152T1 publication Critical patent/ATE149152T1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
    • C07C209/70—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton by reduction of unsaturated amines
    • C07C209/72—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton by reduction of unsaturated amines by reduction of six-membered aromatic rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)

Abstract

This invention relates to an improved process for the preparation of methylcyclohexane diamine wherein meta-toluenediamine is contacted with hydrogen in the presence of a hydrogenation catalyst. The improvement resides in utilizing a hydrogenation catalyst comprising rhodium carried on a support and carrying out the hydrogenation in the presence of a C3-C10 secondary alcohol as a solvent. With the use of rhodium carried on a support as a catalyst, coupled with the use of the secondary alcohol solvent, one obtains high yields with excellent catalyst life.
AT94114878T 1993-09-27 1994-09-21 HYDROGENATION OF META-TOLVENEDIAMINE ATE149152T1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US08/127,659 US5973207A (en) 1993-09-27 1993-09-27 Hydrogenation of meta-toluenediamine

Publications (1)

Publication Number Publication Date
ATE149152T1 true ATE149152T1 (en) 1997-03-15

Family

ID=22431232

Family Applications (1)

Application Number Title Priority Date Filing Date
AT94114878T ATE149152T1 (en) 1993-09-27 1994-09-21 HYDROGENATION OF META-TOLVENEDIAMINE

Country Status (4)

Country Link
US (1) US5973207A (en)
EP (1) EP0645367B1 (en)
AT (1) ATE149152T1 (en)
DE (1) DE69401798T2 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6429338B1 (en) * 2002-01-17 2002-08-06 Air Products And Chemicals, Inc. Hydrogenation of single ring aromatic diamines
DE102004061608A1 (en) * 2004-12-17 2006-07-06 Basf Ag Process for the preparation of 1,2-diamino-3-methylcyclohexane and / or 1,2-diamino-4-methylcyclohexane
CN104177262B (en) * 2014-07-15 2016-08-24 景县本源精化有限公司 The preparation method of aliphatic cyclic amine firming agent

Family Cites Families (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA839281A (en) * 1970-04-14 E.I. Du Pont De Nemours And Company Catalytic hydrogenation process utilizing ruthenium supported on calcium carbonate or a rare earth oxide
CA892636A (en) * 1972-02-08 V. Norton Richard Reduction of aromatic amines
US2606928A (en) * 1947-11-18 1952-08-12 Du Pont Preparation of amino alicyclic compounds
US2511028A (en) * 1947-12-04 1950-06-13 Du Pont 4-[(para-aminophenyl) alkyl] cyclo-hexylamine
US2606924A (en) * 1949-06-09 1952-08-12 Du Pont Bis (4-aminocyclohexyl)-methane
US2606925A (en) * 1949-12-15 1952-08-12 Du Pont Ruthenium catalyzed hydrogenation process for obtaining aminocyclohexyl compounds
US3347917A (en) * 1961-12-29 1967-10-17 Du Pont Process for the preparation of di (paraaminocyclohexyl) methane
US3155724A (en) * 1961-12-29 1964-11-03 Du Pont Process for bringing stereoisomeric mixture of bis-(4-aminocyclohexane) methane close to the equilibrium concentration
US3450759A (en) * 1965-09-07 1969-06-17 Mobay Chemical Corp Preparation of cycloaliphatic diamines free of 0-diamines
US3636108A (en) * 1965-12-23 1972-01-18 Du Pont Catalytic hydrogenation of aromatic nitrogen containing compounds over alkali moderated ruthenium
US3445516A (en) * 1966-01-28 1969-05-20 Mobay Chemical Corp Reduction of tolylene diamines
US3766272A (en) * 1972-08-25 1973-10-16 Du Pont 4,4'-methylenedi(cyclohexylamine)isomerization over a supported catalyst
US3856862A (en) * 1973-06-25 1974-12-24 Upjohn Co Process for hydrogenation of di(4-aminophenyl)methane with a rhodium catalyst
US3914307A (en) * 1973-12-27 1975-10-21 Universal Oil Prod Co Hydrogenation of aromatic amines
US3959374A (en) * 1974-05-30 1976-05-25 Jefferson Chemical Company, Inc. Process for the preparation of mixed isomeric methylene-bridged polycyclohexylpolyamines
CA1204785A (en) * 1981-06-01 1986-05-20 Gary F. Allen Process for the catalytic hydrogenation of di (4- aminophenyl) methane
US4754070A (en) * 1986-01-23 1988-06-28 Air Products And Chemicals, Inc. Hydrogenation of methylenedianiline to produce bis(para-aminocyclohexyl)methane
US4960941A (en) * 1988-03-30 1990-10-02 Air Products And Chemicals, Inc. Hydrogenation of aromatic amines to produce their ring hydrogenated counterparts
US5026914A (en) * 1989-04-11 1991-06-25 Air Products And Chemicals, Inc. Hydrogenation of aromatic amines using rhodium on titania or zirconia support
US5214212A (en) * 1992-02-27 1993-05-25 Olin Corporation Promoters for hydrogenation of aromatic amines

Also Published As

Publication number Publication date
US5973207A (en) 1999-10-26
DE69401798T2 (en) 1997-06-05
EP0645367B1 (en) 1997-02-26
DE69401798D1 (en) 1997-04-03
EP0645367A1 (en) 1995-03-29

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Legal Events

Date Code Title Description
UEP Publication of translation of european patent specification
REN Ceased due to non-payment of the annual fee